HU181870B - Process for producing insecticide-containing microcapsules - Google Patents

Process for producing insecticide-containing microcapsules Download PDF

Info

Publication number: HU181870B
Authority: HU; Hungary
Prior art keywords: microcapsules; methomyl; priority; methylene chloride; viii
Prior art date: 1978-08-03

Application number

HU79DU313A

Other languages

English (en)

Hungarian (hu)

Inventor

Robert T Roche

Original Assignee

Du Pont

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1978-08-03

Filing date

1979-08-03

Publication date

1983-11-28

1979-08-03 Application filed by Du Pont filed Critical Du Pont

1983-11-28 Publication of HU181870B publication Critical patent/HU181870B/hu

Links

239000003094 microcapsule Substances 0.000 title claims abstract description 55
239000002917 insecticide Substances 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 72
UHXUZOCRWCRNSJ-QPJJXVBHSA-N methomyl Chemical compound CNC(=O)O\N=C(/C)SC UHXUZOCRWCRNSJ-QPJJXVBHSA-N 0.000 claims abstract description 48
239000005916 Methomyl Substances 0.000 claims abstract description 46
239000000203 mixture Substances 0.000 claims abstract description 41
239000005056 polyisocyanate Substances 0.000 claims abstract description 14
229920001228 polyisocyanate Polymers 0.000 claims abstract description 14
229920002396 Polyurea Polymers 0.000 claims abstract description 13
229920000768 polyamine Polymers 0.000 claims abstract description 11
150000004985 diamines Chemical class 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims abstract description 8
230000001804 emulsifying effect Effects 0.000 claims abstract description 5
239000004094 surface-active agent Substances 0.000 claims description 15
239000004480 active ingredient Substances 0.000 claims description 12
125000005442 diisocyanate group Chemical group 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
239000002775 capsule Substances 0.000 claims description 11
229920000642 polymer Polymers 0.000 claims description 10
229920002451 polyvinyl alcohol Polymers 0.000 claims description 10
239000012948 isocyanate Substances 0.000 claims description 9
150000002513 isocyanates Chemical class 0.000 claims description 9
-1 methylcarbamoyl Chemical group 0.000 claims description 8
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical group NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
239000000839 emulsion Substances 0.000 claims description 7
235000019422 polyvinyl alcohol Nutrition 0.000 claims description 6
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 6
239000004372 Polyvinyl alcohol Substances 0.000 claims description 5
238000002156 mixing Methods 0.000 claims description 5
239000000725 suspension Substances 0.000 claims description 5
239000004793 Polystyrene Substances 0.000 claims description 4
229920002223 polystyrene Polymers 0.000 claims description 4
229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 claims description 2
229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 2
239000004926 polymethyl methacrylate Substances 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims 1
125000003916 ethylene diamine group Chemical group 0.000 claims 1
238000011065 in-situ storage Methods 0.000 claims 1
KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 abstract description 16
239000005950 Oxamyl Substances 0.000 abstract description 13
230000000749 insecticidal effect Effects 0.000 abstract description 12
239000000243 solution Substances 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
241000196324 Embryophyta Species 0.000 description 11
238000009472 formulation Methods 0.000 description 11
239000002245 particle Substances 0.000 description 11
239000012074 organic phase Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 9
239000008346 aqueous phase Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
241000238631 Hexapoda Species 0.000 description 6
CVRALZAYCYJELZ-UHFFFAOYSA-N O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate Chemical compound C=1C=CC=CC=1P(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl CVRALZAYCYJELZ-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000003085 diluting agent Substances 0.000 description 6
NYPJDWWKZLNGGM-UHFFFAOYSA-N fenvalerate Chemical compound C=1C=C(Cl)C=CC=1C(C(C)C)C(=O)OC(C#N)C(C=1)=CC=CC=1OC1=CC=CC=C1 NYPJDWWKZLNGGM-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 5
150000001875 compounds Chemical class 0.000 description 5
230000001069 nematicidal effect Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
AIGRXSNSLVJMEA-UHFFFAOYSA-N EPN Chemical compound C=1C=CC=CC=1P(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 AIGRXSNSLVJMEA-UHFFFAOYSA-N 0.000 description 4
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 4
229960005286 carbaryl Drugs 0.000 description 4
OWZREIFADZCYQD-NSHGMRRFSA-N deltamethrin Chemical compound CC1(C)[C@@H](C=C(Br)Br)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 OWZREIFADZCYQD-NSHGMRRFSA-N 0.000 description 4
QQQYTWIFVNKMRW-UHFFFAOYSA-N diflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC=C(Cl)C=C1 QQQYTWIFVNKMRW-UHFFFAOYSA-N 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
238000006116 polymerization reaction Methods 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
229920000742 Cotton Polymers 0.000 description 3
239000005893 Diflubenzuron Substances 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
241000219146 Gossypium Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
241000244206 Nematoda Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
QGLZXHRNAYXIBU-WEVVVXLNSA-N aldicarb Chemical compound CNC(=O)O\N=C\C(C)(C)SC QGLZXHRNAYXIBU-WEVVVXLNSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000007900 aqueous suspension Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
229960002483 decamethrin Drugs 0.000 description 3
229940019503 diflubenzuron Drugs 0.000 description 3
238000004806 packaging method and process Methods 0.000 description 3
RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 3
RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 3
229960000490 permethrin Drugs 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000012360 testing method Methods 0.000 description 3
RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 3
239000004563 wettable powder Substances 0.000 description 3
239000005946 Cypermethrin Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
231100000674 Phytotoxicity Toxicity 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 description 2
229960005424 cypermethrin Drugs 0.000 description 2
YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000005538 encapsulation Methods 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000012530 fluid Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000178 monomer Substances 0.000 description 2
239000005645 nematicide Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
239000002689 soil Substances 0.000 description 2
241000894007 species Species 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
YFOOEYJGMMJJLS-UHFFFAOYSA-N 1,8-diaminonaphthalene Chemical compound C1=CC(N)=C2C(N)=CC=CC2=C1 YFOOEYJGMMJJLS-UHFFFAOYSA-N 0.000 description 1
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
235000016068 Berberis vulgaris Nutrition 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
239000001836 Dioctyl sodium sulphosuccinate Substances 0.000 description 1
240000002024 Gossypium herbaceum Species 0.000 description 1
235000004341 Gossypium herbaceum Nutrition 0.000 description 1
239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241001477931 Mythimna unipuncta Species 0.000 description 1
UOBDMUFIOFAEMI-UHFFFAOYSA-N N=C=O.N=C=O.O=C=NC(C(Cl)=C(C(Cl)=C1N=C=O)Cl)=C1Cl.ClC(C1=CC=CC=C1)(C1=CC=CC=C1)Cl Chemical compound N=C=O.N=C=O.O=C=NC(C(Cl)=C(C(Cl)=C1N=C=O)Cl)=C1Cl.ClC(C1=CC=CC=C1)(C1=CC=CC=C1)Cl UOBDMUFIOFAEMI-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
241001509980 Shelfordella lateralis Species 0.000 description 1
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
230000000895 acaricidal effect Effects 0.000 description 1
239000000642 acaricide Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000003254 anti-foaming effect Effects 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000003899 bactericide agent Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007797 corrosion Effects 0.000 description 1
238000005260 corrosion Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003599 detergent Substances 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000003966 growth inhibitor Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
231100001225 mammalian toxicity Toxicity 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 1
KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
235000021278 navy bean Nutrition 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
GVDMJXQHPUYPHP-FYQPLNBISA-N norgestrienone Chemical compound C1CC(=O)C=C2CC[C@@H]([C@H]3[C@@](C)([C@](CC3)(O)C#C)C=C3)C3=C21 GVDMJXQHPUYPHP-FYQPLNBISA-N 0.000 description 1
239000007764 o/w emulsion Substances 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000006174 pH buffer Substances 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000003307 slaughter Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
229960001124 trientine Drugs 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Agronomy & Crop Science (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Toxicology (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

HU79DU313A 1978-08-03 1979-08-03 Process for producing insecticide-containing microcapsules HU181870B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US93076078A	1978-08-03	1978-08-03
US4219179A	1979-05-29	1979-05-29

Publications (1)

Publication Number	Publication Date
HU181870B true HU181870B (en)	1983-11-28

Family

ID=26718967

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU79DU313A HU181870B (en)	1978-08-03	1979-08-03	Process for producing insecticide-containing microcapsules

Country Status (23)

Country	Link
EP (1)	EP0008207B1 (da)
AU (1)	AU527286B2 (da)
BG (2)	BG31481A3 (da)
BR (1)	BR7904857A (da)
CA (1)	CA1131560A (da)
DE (1)	DE2961508D1 (da)
DK (1)	DK253779A (da)
EG (1)	EG14188A (da)
ES (1)	ES483119A1 (da)
GB (1)	GB2027346B (da)
GR (1)	GR69852B (da)
HU (1)	HU181870B (da)
IL (1)	IL57960A (da)
KE (1)	KE3263A (da)
MA (1)	MA18551A1 (da)
NO (1)	NO792544L (da)
NZ (1)	NZ191195A (da)
OA (1)	OA06309A (da)
PH (1)	PH15548A (da)
PT (1)	PT70017A (da)
RO (1)	RO77008A (da)
TR (1)	TR20266A (da)
ZM (1)	ZM6679A1 (da)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4280833A (en) *	1979-03-26	1981-07-28	Monsanto Company	Encapsulation by interfacial polycondensation, and aqueous herbicidal composition containing microcapsules produced thereby
ATE77916T1 (de) *	1985-09-13	1992-07-15	Ciba Geigy Ag	Verfahren zur herstellung von mikrokapseln.
US5229122A (en) *	1986-02-07	1993-07-20	Burroughs Wellcome Co.	Pesticidal compositions
GB8603061D0 (en) *	1986-02-07	1986-03-12	Wellcome Found	Pesticidal formulations
ATE101483T1 (de) *	1986-07-09	1994-03-15	Monsanto Co	Formulierungen von wasserdispergierbaren granulaten und verfahren zu deren herstellung.
JPH0818937B2 (ja) *	1987-07-06	1996-02-28	住友化学工業株式会社	農園芸用有機燐系殺虫組成物
JP2524201B2 (ja) *	1988-08-22	1996-08-14	日本特殊陶業株式会社	窒化珪素質焼結体及びその製造方法
MY107070A (en) *	1988-11-11	1995-09-30	Sumitomo Chemical Co	Improved pesticidal composition
GB8827029D0 (en) *	1988-11-18	1988-12-21	Ici Plc	Insecticidal compositions
US5223477A (en) *	1989-02-03	1993-06-29	Imperial Chemical Industries Plc	Single-package agricultural formulations combining immediate and time-delayed delivery of thiocarbamate herbicides and dichlormid as safener
US5049182A (en) *	1989-02-03	1991-09-17	Ici Americas Inc.	Single-package agricultural formulations combining immediate and time-delayed delivery
NZ235752A (en) *	1989-11-10	1993-02-25	Sumitomo Chemical Co	Pesticidal compositions containing a suspended pyrethroid and a microencapsulated organophosphorus compound and/or carbamate, in water
US5526607A (en) *	1991-08-15	1996-06-18	Net/Tech International	Water dispersible delivery system for an agriculturally active chemical
US5335449A (en) *	1991-08-15	1994-08-09	Net/Tech International, Inc.	Delivery system for an agriculturally active chemical
CN1059777C (zh) *	1994-06-01	2000-12-27	西北农业大学	一种除虫脲复配乳油杀虫剂及其生产方法
FR2746261B1 (fr) *	1996-03-19	1998-05-07	Virbac Sa	Composition insecticide et procede de preparation
ES2127120B1 (es) *	1996-12-23	1999-11-16	Herrero Maria Pilar Mateo	Pinturas inhibidoras de la sintesis de quintina de los artropodos para el control de plagas y alergenos.
US6992047B2 (en) *	2001-04-11	2006-01-31	Monsanto Technology Llc	Method of microencapsulating an agricultural active having a high melting point and uses for such materials
RU2212797C2 (ru) *	2001-12-05	2003-09-27	Общество с ограниченной ответственностью "Дезстанция "Ромашка"	Способ получения препарата для уничтожения бытовых насекомых в виде водной суспензии на основе микрокапсулированного раствора хлорпирифоса
FR2850880B1 (fr) *	2003-02-07	2006-06-23	Cerexagri	Fabrication de microbilles de pesticides et utilisation de ces microbilles dans la protection des cultures
PL2395843T3 (pl)	2009-02-13	2018-01-31	Monsanto Technology Llc	Kapsułkowanie herbicydów do zmniejszenia uszkodzeń upraw
CN101869115A (zh) *	2009-04-23	2010-10-27	迟德富	纳米除虫脲微胶囊制备方法
PL2605646T3 (pl)	2010-08-18	2017-01-31	Monsanto Technology Llc	Wczesne zastosowanie kapsułkowych pochodnych acetamidu w celu zmniejszenia uszkodzeń upraw
MX383040B (es)	2014-01-27	2025-03-13	Monsanto Technology Llc	Concentrados herbicidas acuosos.
JP6862415B2 (ja)	2015-07-24	2021-04-21	ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆＳｅ	植物病原性菌類の駆除に有用なピリジン化合物
CR20180194A (es)	2015-09-03	2018-09-03	Basf Agro Bv	Composiciones de microparticulas que comprenden saflufenacil
MX2019015014A (es)	2017-06-13	2020-02-26	Monsanto Technology Llc	Herbicidas microencapsulados.
UA129154C2 (uk)	2019-01-30	2025-01-29	Монсанто Текнолоджі Ллс	Мікрокапсульовані ацетамідні гербіциди
EP4011205A1 (en)	2020-12-08	2022-06-15	Basf Se	Microparticle compositions comprising trifludimoxazin
EP4011208A1 (en)	2020-12-08	2022-06-15	BASF Corporation	Microparticle compositions comprising fluopyram

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3577515A (en) *	1963-12-13	1971-05-04	Pennwalt Corp	Encapsulation by interfacial polycondensation
DE2017808A1 (en) *	1970-04-14	1971-10-21	Erz und Kohleflotation GmbH, 4630 Bochum	Microencapsulated pesticides compns
IE35170B1 (en) *	1970-04-28	1975-11-26	Fuji Photo Film Co Ltd	Process for the production of oily liquid-containing microcapsules
CA1104882A (en) *	1972-03-15	1981-07-14	Herbert B. Scher	Encapsulation process

1979
- 1979-06-18 DK DK253779A patent/DK253779A/da unknown
- 1979-07-30 BR BR7904857A patent/BR7904857A/pt unknown
- 1979-08-01 EG EG467/79A patent/EG14188A/xx active
- 1979-08-01 RO RO7998332A patent/RO77008A/ro unknown
- 1979-08-01 MA MA18749A patent/MA18551A1/fr unknown
- 1979-08-01 CA CA333,004A patent/CA1131560A/en not_active Expired
- 1979-08-02 AU AU49504/79A patent/AU527286B2/en not_active Ceased
- 1979-08-02 PH PH22843A patent/PH15548A/en unknown
- 1979-08-02 NO NO792544A patent/NO792544L/no unknown
- 1979-08-02 NZ NZ191195A patent/NZ191195A/xx unknown
- 1979-08-02 IL IL57960A patent/IL57960A/xx unknown
- 1979-08-02 OA OA56864A patent/OA06309A/xx unknown
- 1979-08-02 PT PT70017A patent/PT70017A/pt unknown
- 1979-08-02 TR TR20266A patent/TR20266A/xx unknown
- 1979-08-03 DE DE7979301568T patent/DE2961508D1/de not_active Expired
- 1979-08-03 BG BG048676A patent/BG31481A3/xx unknown
- 1979-08-03 BG BG044550A patent/BG31480A3/xx unknown
- 1979-08-03 GB GB7927101A patent/GB2027346B/en not_active Expired
- 1979-08-03 HU HU79DU313A patent/HU181870B/hu unknown
- 1979-08-03 ZM ZM66/79A patent/ZM6679A1/xx unknown
- 1979-08-03 EP EP79301568A patent/EP0008207B1/en not_active Expired
- 1979-08-03 GR GR59768A patent/GR69852B/el unknown
- 1979-08-03 ES ES483119A patent/ES483119A1/es not_active Expired
1983
- 1983-02-25 KE KE3263A patent/KE3263A/xx unknown

Also Published As

Publication number	Publication date
GB2027346B (en)	1982-08-04
KE3263A (en)	1983-03-25
GR69852B (da)	1982-07-19
OA06309A (fr)	1981-06-30
IL57960A0 (en)	1979-12-30
EP0008207A2 (en)	1980-02-20
NO792544L (no)	1980-02-05
BG31480A3 (en)	1982-01-15
AU4950479A (en)	1980-02-07
RO77008A (ro)	1981-08-30
ES483119A1 (es)	1980-09-01
EP0008207B1 (en)	1981-12-02
NZ191195A (en)	1981-12-15
DK253779A (da)	1980-02-04
MA18551A1 (fr)	1980-04-01
IL57960A (en)	1982-04-30
BR7904857A (pt)	1980-05-06
PT70017A (en)	1979-09-01
PH15548A (en)	1983-02-09
GB2027346A (en)	1980-02-20
AU527286B2 (en)	1983-02-24
ZM6679A1 (en)	1981-02-23
EP0008207A3 (en)	1980-03-05
TR20266A (tr)	1980-12-08
BG31481A3 (en)	1982-01-15
DE2961508D1 (en)	1982-01-28
CA1131560A (en)	1982-09-14
EG14188A (en)	1983-12-31

Publication	Publication Date	Title
EP0008207B1 (en)	1981-12-02	Insecticidal compositions, and preparation and use thereof
EP1282353B2 (de)	2009-04-29	Kombinationen von pflanzenschutzmitteln mit organischen oder anorganischen trägermaterialien
FI67789C (fi)	1985-06-10	Foerfarande foer inkapsling av ett med vatten oblandbart material
US4235872A (en)	1980-11-25	Microencapsulated methomyl insecticide
JP3419871B2 (ja)	2003-06-23	マイクロカプセルの製造方法
AU734072B2 (en)	2001-05-31	Microcapsules with readily adjustable release rates
EP0005302B1 (en)	1981-11-25	Impregnated porous granules with slow-release pore membranes, and process for the manufacture thereof
CN1104277C (zh)	2003-04-02	微胶囊化的组合物
HU215771B (hu)	2000-09-28	2-Klór-N-(etoxi-metil)-6'-etil-o-aceto-toluidid herbicidet tartalmazó kapszulák és eljárás előállításukra
DK149341B (da)	1986-05-12	Fremgangsmaade til indkapsling af hydrofobe stoffer ved graensefladepolykondensation
FR2920271A1 (fr)	2009-03-06	Composition pesticide
US9622473B2 (en)	2017-04-18	Herbicidal compositions
KR20110132354A (ko)	2011-12-07	향상된 잔류 활성을 갖는 마이크로캡슐화 살충제
DE69124369T2 (de)	1997-05-15	Imprägnierte poröse granulate für gesteuerte abgabe von fliessfähigem material und verfahren zu ihrer herstellung
KR850001266B1 (ko)	1985-09-04	식물독성이 감소된 살충제 조성물의 제법
EA018830B1 (ru)	2013-11-29	Стабилизированные препараты микрокапсул карбофоса
JPH02188506A (ja)	1990-07-24	殺アブラムシ剤組成物、その製造方法及びアブラムシの防除方法
KR20110091747A (ko)	2011-08-12	농약 함유 수지 조성물의 제조 방법
KR830001488B1 (ko)	1983-08-03	살충제 조성물의 제조방법
DD142274A5 (de)	1980-06-18	Herbizides mittel
RU99123179A (ru)	2001-09-27	Способ капсулирования и капсулированные продукты
BE874897A (fr)	1979-07-16	Trifluraline microencapsulee
HK1020690B (en)	2003-11-28	Microencapsulated compositions